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couple, selfie, adler, planetarium, Adler Planetarium
Photograph: Courtesy Adler Planetarium

19 romantic things to do in Chicago

Crank the heat on your next date night with the most romantic things to do in Chicago

By Morgan Olsen, Kris Vire and Grace Perry

Believe it or not, Chicago is brimming with romance. And possibly even more so for all the amorous pleasantries that go unseen during our brutal winters—in sweatpants, under blankets in our heated apartments with Netflix rolling in the background. When the weather permits, though, city-dwelling couples come of out hibernation in search of romantic things to do in Chicago. After you've exhausted the most romantic restaurants in Chicago, it's time to get creative. Turn your attention to some of the top-rated Chicago attractions for inspiration. Suddenly, the conservatory is an exotic oasis and the old-timey movie theater offers an excuse to curl up close. Whether you're celebrating Valentine's Day in Chicago or you're just planning a date night, turn up the heat with the most romantic things to do Chicago.

The most romantic things to do in Chicago

Buckingham Fountain
Rob Pongsajapan/Flickr

1. Buckingham Fountain

Things to do Grant Park

With its four Art Deco-style seahorses, Georgia pink marble and light and music show, this fountain built in 1927 is a sight to behold and a great backdrop for some twilight smooching. From April through mid-October (depending on weather), 20-minute shows every hour on the hour feature 14,000 gallons of water spouting from 133 jets. In summer, see the nighttime colored light shows, capped off with a center jet shooting water 150 feet in the air.

Chicago skyline from Promontory Point
Photograph: Courtesy CC/Flickr/JohnPickenPhoto

2. Promontory Point

Things to do Hyde Park

There's a good chance that you know at least one person who has considered getting hitched on Promontory Point, a man-made peninsula on the shore of Lake Michigan. Accessible via the Lakefront Trail, the park boasts amazing views of the Chicago skyline and a field house that could be mistaken for a small castle.

garfield park conservatory
Photograph: Time Out/Jaclyn Rivas

3. Garfield Park Conservatory

Attractions Parks and gardens East Garfield Park

Described as “landscape art under glass” when it opened in 1908, the conservatory, while being one of the largest in the world, also boasts revolutionary architecture. With the building’s haystack shape and walls of stratified stonework, landscape architect Jens Jensen considered the Fern Room in particular, with its “prairie waterfall”—a stone and water element within a glass structure—to be one of his greatest achievements. When winter rolls around, the 120,000 lush plants that populate the space make a great backdrop for a date. Sneak a kiss in the Desert House or stroll through the Aroid House hand in hand.

Photograph: Juan Serano Corbella

4. Aire Ancient Baths

Health and beauty River West/West Town

Breathing new life into the ancient tradition of Greek and Roman bath houses, Aire Ancient Baths is a singular spa experience that can be enjoyed solo or with a partner. Book a couples massage or body treatment and make time to explore the spa's different baths, which vary from ice-cold to steaming hot.

The ice ribbon at Maggie Daley Park.
Photograph: Martha Williams

5. Maggie Daley Park Skating Ribbon

Attractions Parks and gardens Millennium Park

If you don't mind sharing personal space with kiddos, dust off your ice skates (or rent a pair onsite) and hit the winding rink at Maggie Daley Park in the heart of downtown Chicago. Hold your honey's hand as you make your way around the circular path set against skyline views. After you've worked up a sweat, grab steamy cocktails at a nearby bar.

Photograph: Max Herman

6. Music Box Theatre

Movie theaters Independent Wrigleyville

For movie lovers who don't care for traditional Hollywood blockbusters, there's no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. It's gorgeous, and the main theater regularly hosts director Q&A's as well as weekly midnight screenings of cult classics. Also, the concession stand here tops its popcorn with real butter.

Photograph: Neal O'Bryan

7. Centennial Wheel at Navy Pier

Attractions Towers and viewpoints Streeterville

For most locals, Navy Pier can feel like a tourist trap, but there's no denying the romantic appeal of a 200-foot-tall Ferris wheel with bird's-eye views of the city skyline and Lake Michigan. Each ride lasts about 15 minutes (giving you just enough time to cuddle up with your partner), and you can splurge on a Fast Pass ticket to skip the line and the crowds.

Alfred Caldwell Lily Pool
Photograph: Courtesy Lincoln Park Conservatory

8. Alfred Caldwell Lily Pool

Things to do Lincoln Park

Accessible from April to November, this semi-hidden oasis inside Lincoln Park has become a popular venue for small weddings since it was restored and reopened in 2002. But you don't have to be getting hitched to enjoy the spot's naturally romantic vibe.

emporium, fulton market
Photograph: Jaclyn Rivas

9. Emporium Arcade Bar

Bars Beer bars Wicker Park

Whether it's your first date or your 400th, Emporium Arcade Bar offers interactive fun to break up date-night monotony. Face off against your partner in Mortal Kombat, take turns playing Ms. Pac-Man or clean the table with a round of pool. As an added bonus, all Emporium locations allow guests to bring in outside food, so you can add dinner to the mix, too.

10. Adler Planetarium

Museums Science and technology Museum Campus

There's a reason so many Chicagoans take their engagement photos at this institution. Situated at the outermost point of the Museum Campus peninsula, the Adler boasts specular skyline views—arguably the best in the city. But the building itself ain't too shabby, either. Opened in 1930 as the first planetarium in North America, the Adler is a National Historic Landmark. Make it a date night at the museum's monthly 21+ series, Adler After Dark, which features wine, beer, and lots of fun factoids about the night sky.

Photograph: Maarten van den Heuvel

11. Chicago Theatre

Music Music venues Loop

The Loop’s 5,000-seat Chicago Theatre was the opulent French baroque-style flagship of the Balaban and Katz movie palace chain when it opened in 1921. It’s still a beautiful venue (you’ve probably seen the famous illuminated Chicago marquee even if you’re from out of town) that’s surprisingly cozy for its large size.

Photograph: Chicago Athletic Association

12. Chicago Athletic Association

Hotels Boutique hotels Loop

Whether you're checking in for a romantic staycation or you're exploring the storied hotel's public-facing bars and restaurants, there's no shortage of charm at this luxury boutique property. Take in unparalleled city views from Cindy's rooftop, splurge on a special meal at Cherry Circle Room, face off in the Game Room or split an order of fries at Shake Shack—the possibilities are endless.

Photograph: Martha Williams

13. Chicago Cultural Center

Museums Art and design Loop

We know what you're thinking: The Chicago Cultural Center? Romantic? But just go with us on this one. After exploring the building's galleries, make your way to Preston Bradley Hall to see the building’s architectural crown jewel, a stained-glass Tiffany dome that stretches 38 feet in diameter. The best way to view it is by lying on the ground with someone you love and gazing up (don't worry—plenty of folks do it!). 

Harold Washington Library Winter Reading Room
Courtesy CC/Flickr/Spiro Bolos

14. Harold Washington Library Center Winter Garden

Attractions Libraries, archives and foundations Loop

The ninth floor of the Harold Washington Library Center is one of Chicago's unsung gems. In what is otherwise a labyrinthian network of hallways and books reminiscent of Chicago's iconic bureaucracy, on the library's topmost floor is the Winter Garden, perfect for a couple to share a reprieve of peaceful quietude immersed in literature and fantastic surroundings.

Thalia Hall
Photograph: Clayton Hauck

15. Thalia Hall

Music Music venues Lower West Side

For music lovers, there's no more romantic spot in Chicago than this Pilsen concert venue. Initially opened as a bohemian opera house in 1892, the refurbished Thalia Hall hosts touring bands nearly every night of the week. It retains that 19th century charm with original molding around the stage, chipping paint and opera boxes flanking the stage. Up the ante with drinks at Punch House, the hip bar in the venue's basement, or take in an evening of cabaret at Tack Room, just adjacent. 

Moon Bridge, Osaka Garden ("Japanese Garden", Wooded Island, Jackson Park, Chicago
Photograph: Steven Kevil/Wiki Commons

16. The Garden of the Phoenix in Jackson Park

Things to do Literary events Woodlawn

Initially designed by Frederick Law Olmsted for the World's Columbian Exposition of 1893, Jackson Park is one of the city's crown jewels. But perhaps its most enchanting section is the Garden of the Phoenix, a Japanese strolling garden on Wooded Island. Formally known as the Osaka Garden (for Chicago's sister city), the grounds now feature a permanent art installation by Yoko Ono. It's the perfect place to saunter through with someone special.


17. The Green Mill

Bars Cocktail bars Uptown

Al Capone and other gangsters used to hang here in the 1920s, but these days it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop and free jazz with a discriminating ear. Grab a booth, order a round of drinks and prepare to tap your toes with your favorite human.

lincoln park zoo lemur
Photograph: Chris Bijalba/Lincoln Park Zoo

18. Lincoln Park Zoo

Things to do Lincoln Park

See some 1,200 animals, from apes to zebras, at the oldest and one of only a few free zoos left in the country. Locals know that the attraction is open all year, with ZooLights taking over in the winter months and events like Craft Brews at the Zoo offered in the summer. No matter the season, you and your date can see aardvarks, howler monkeys, polar bears and snakes.

Photograph: Jeremy Atherton

19. Chicago Riverwalk

Things to do Loop

Any couple looking for a stroll packed with relaxing scenery and breathtaking views of some of Chicago's most beautiful architecture should take a romantic jaunt along the Riverwalk. A series of public walkways and seating areas offers access to boat tours and water taxis as well as waterfront cafes and restaurants.


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